Ethyl chloroformate → 5-Ethoxycarbonylamino-2-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)fluorobenzene

HRID 1167451Notes

Reaction equation

HRID 1167451 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[C:6]([F:8])[CH:7]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>N1C=CC=CC=1>[CH2:26]([O:25][C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[C:6]([F:8])[CH:7]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 20725688HCID 20725688, compound

Product 1

HCID 207256905-Ethoxycarbonylamino-2-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)fluorobenzene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-2-((3R)-3-t-butoxycarbonylamino-1-pyrrolidinyl)fluorobenzene (27.33 g, 0.093 M) was dissolved in dry pyridine (150 ml) and cooled under nitrogen with stirring to 0°. Ethyl chloroformate (11.01, 0.102 M) was added dropwise, and the mixture stirred 30 minutes at the same temperature. Ice-water (250 ml) was added, and stirring continued for 1 hour. The resulting precipitate was collected, washed thoroughly with water, and dried, to give the desired product of sufficient quality for use without purification (33.6 g). MS (ESP): 368 (MH+) for C18H26FN3O4.

Workup

  1. temperaturecooled under nitrogen
  2. stirringthe mixture stirred 30 minutes at the same temperature
  3. stirringstirring
  4. customThe resulting precipitate was collected
  5. washwashed thoroughly with water
  6. customdried

Sources & evidence

ORD record
ord-0f0f0db779aa482480f5cc3f044a9ffb
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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